#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017993.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017993
loop_
_publ_author_name
'Fang, Chao'
'Ma, Jian-Ping'
'Wei, Sui'
'Dong, Yu-Bin'
_publ_section_title
;
 1,1'-[(Ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline-2,3-dione)
 (L) and a novel [Ag₂L₂]²⁺ metallocycle based on
 coordination-driven Ag---O and Ag---π bonds
;
_journal_coeditor_code           SQ3280
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m35
_journal_page_last               m38
_journal_paper_doi               10.1107/S0108270110054697
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C32 H24 N2 O6'
_chemical_formula_moiety         'C32 H24 N2 O6'
_chemical_formula_sum            'C32 H24 N2 O6'
_chemical_formula_weight         532.53
_chemical_name_systematic
;
1,1'-[(Ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline-2,3-dione)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.472(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8272(17)
_cell_length_b                   14.194(5)
_cell_length_c                   18.883(7)
_cell_measurement_reflns_used    857
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.884
_cell_measurement_theta_min      2.591
_cell_volume                     1293.4(8)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6683
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bar
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1097
_refine_ls_R_factor_gt           0.0651
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0677P)²+0.1059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1604
_reflns_number_gt                1506
_reflns_number_total             2398
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sq3280.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017993
_cod_database_fobs_code          2017993
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0460(6) 0.34667(18) 0.22697(14) 0.0505(7) Uani d . 1 . .
C C2 -0.1003(6) 0.2714(2) 0.25147(15) 0.0648(8) Uani d . 1 . .
H H2 -0.0792 0.2113 0.2328 0.078 Uiso calc R 1 . .
C C3 -0.2851(7) 0.2899(3) 0.30652(17) 0.0831(11) Uani d . 1 . .
H H3 -0.3859 0.2403 0.3252 0.100 Uiso calc R 1 . .
C C4 -0.3202(8) 0.3788(3) 0.33323(18) 0.0871(11) Uani d . 1 . .
H H4 -0.4466 0.3886 0.3688 0.105 Uiso calc R 1 . .
C C5 -0.1735(8) 0.4526(3) 0.30853(18) 0.0816(11) Uani d . 1 . .
H H5 -0.1965 0.5128 0.3269 0.098 Uiso calc R 1 . .
C C6 0.0111(6) 0.4361(2) 0.25532(15) 0.0604(8) Uani d . 1 . .
C C7 0.1959(7) 0.4991(2) 0.21878(16) 0.0711(9) Uani d . 1 . .
C C8 0.3527(7) 0.4360(2) 0.16718(16) 0.0621(8) Uani d . 1 . .
C C9 0.3228(6) 0.26742(19) 0.13121(14) 0.0562(8) Uani d . 1 . .
H H9A 0.3734 0.2157 0.1626 0.067 Uiso calc R 1 . .
H H9B 0.4857 0.2840 0.1049 0.067 Uiso calc R 1 . .
C C10 0.1012(6) 0.23380(17) 0.07975(13) 0.0471(7) Uani d . 1 . .
C C11 0.0150(6) 0.14134(19) 0.07931(15) 0.0593(8) Uani d . 1 . .
H H11 0.0934 0.0997 0.1121 0.071 Uiso calc R 1 . .
C C12 -0.1832(7) 0.1087(2) 0.03189(18) 0.0701(9) Uani d . 1 . .
H H12 -0.2372 0.0459 0.0329 0.084 Uiso calc R 1 . .
C C13 -0.3014(7) 0.1690(2) -0.01692(17) 0.0683(9) Uani d . 1 . .
H H13 -0.4379 0.1473 -0.0485 0.082 Uiso calc R 1 . .
C C14 -0.2181(6) 0.2615(2) -0.01915(14) 0.0606(8) Uani d . 1 . .
H H14 -0.2956 0.3020 -0.0529 0.073 Uiso calc R 1 . .
C C15 -0.0193(6) 0.29457(17) 0.02871(14) 0.0480(7) Uani d . 1 . .
C C16 -0.0569(7) 0.45357(16) -0.01211(15) 0.0606(8) Uani d . 1 . .
H H16A -0.2558 0.4513 -0.0061 0.073 Uiso calc R 1 . .
H H16B -0.0190 0.4433 -0.0617 0.073 Uiso calc R 1 . .
N N1 0.2453(5) 0.34815(14) 0.17423(11) 0.0510(6) Uani d . 1 . .
O O1 0.2339(6) 0.58289(16) 0.22527(15) 0.1163(10) Uani d . 1 . .
O O2 0.5383(5) 0.46048(15) 0.12861(13) 0.0868(8) Uani d . 1 . .
O O3 0.0785(4) 0.38421(12) 0.03087(10) 0.0592(6) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.0(3) ?
C2 C1 N1 . . 128.4(3) ?
C6 C1 N1 . . 110.6(2) ?
C1 C2 C3 . . 116.5(3) ?
C1 C2 H2 . . 121.8 ?
C3 C2 H2 . . 121.8 ?
C4 C3 C2 . . 121.9(3) ?
C4 C3 H3 . . 119.1 ?
C2 C3 H3 . . 119.1 ?
C5 C4 C3 . . 121.0(4) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
C4 C5 C6 . . 118.2(3) ?
C4 C5 H5 . . 120.9 ?
C6 C5 H5 . . 120.9 ?
C5 C6 C1 . . 121.5(3) ?
C5 C6 C7 . . 131.2(3) ?
C1 C6 C7 . . 107.3(3) ?
O1 C7 C6 . . 130.7(3) ?
O1 C7 C8 . . 124.2(3) ?
C6 C7 C8 . . 105.1(3) ?
O2 C8 N1 . . 127.5(3) ?
O2 C8 C7 . . 126.4(3) ?
N1 C8 C7 . . 106.1(3) ?
N1 C9 C10 . . 114.9(2) ?
N1 C9 H9A . . 108.6 ?
C10 C9 H9A . . 108.6 ?
N1 C9 H9B . . 108.6 ?
C10 C9 H9B . . 108.6 ?
H9A C9 H9B . . 107.5 ?
C11 C10 C15 . . 117.4(3) ?
C11 C10 C9 . . 121.1(2) ?
C15 C10 C9 . . 121.5(2) ?
C12 C11 C10 . . 122.0(3) ?
C12 C11 H11 . . 119.0 ?
C10 C11 H11 . . 119.0 ?
C13 C12 C11 . . 119.9(3) ?
C13 C12 H12 . . 120.0 ?
C11 C12 H12 . . 120.0 ?
C12 C13 C14 . . 120.0(3) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.2(3) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
O3 C15 C14 . . 124.9(2) ?
O3 C15 C10 . . 114.6(2) ?
C14 C15 C10 . . 120.4(2) ?
O3 C16 C16 . 3_565 106.0(3) ?
O3 C16 H16A . . 110.5 ?
C16 C16 H16A 3_565 . 110.5 ?
O3 C16 H16B . . 110.5 ?
C16 C16 H16B 3_565 . 110.5 ?
H16A C16 H16B . . 108.7 ?
C8 N1 C1 . . 110.7(2) ?
C8 N1 C9 . . 124.2(2) ?
C1 N1 C9 . . 125.0(2) ?
C15 O3 C16 . . 118.5(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.368(4) ?
C1 C6 . 1.390(3) ?
C1 N1 . 1.402(3) ?
C2 C3 . 1.412(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.372(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.353(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(5) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.450(4) ?
C7 O1 . 1.209(3) ?
C7 C8 . 1.537(4) ?
C8 O2 . 1.219(4) ?
C8 N1 . 1.358(3) ?
C9 N1 . 1.459(3) ?
C9 C10 . 1.504(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.377(4) ?
C10 C15 . 1.408(3) ?
C11 C12 . 1.374(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.371(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.373(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9300 ?
C15 O3 . 1.357(3) ?
C16 O3 . 1.424(3) ?
C16 C16 3_565 1.495(5) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.2(4) ?
N1 C1 C2 C3 . . . . 178.7(3) ?
C1 C2 C3 C4 . . . . 1.2(5) ?
C2 C3 C4 C5 . . . . -1.3(5) ?
C3 C4 C5 C6 . . . . 0.5(5) ?
C4 C5 C6 C1 . . . . 0.5(5) ?
C4 C5 C6 C7 . . . . -179.6(3) ?
C2 C1 C6 C5 . . . . -0.6(4) ?
N1 C1 C6 C5 . . . . -179.7(3) ?
C2 C1 C6 C7 . . . . 179.4(3) ?
N1 C1 C6 C7 . . . . 0.4(3) ?
C5 C6 C7 O1 . . . . -0.7(6) ?
C1 C6 C7 O1 . . . . 179.2(3) ?
C5 C6 C7 C8 . . . . 178.1(3) ?
C1 C6 C7 C8 . . . . -2.0(3) ?
O1 C7 C8 O2 . . . . 2.6(5) ?
C6 C7 C8 O2 . . . . -176.2(3) ?
O1 C7 C8 N1 . . . . -178.2(3) ?
C6 C7 C8 N1 . . . . 2.9(3) ?
N1 C9 C10 C11 . . . . -125.7(3) ?
N1 C9 C10 C15 . . . . 56.5(3) ?
C15 C10 C11 C12 . . . . -0.8(4) ?
C9 C10 C11 C12 . . . . -178.7(3) ?
C10 C11 C12 C13 . . . . 0.0(4) ?
C11 C12 C13 C14 . . . . 1.1(5) ?
C12 C13 C14 C15 . . . . -1.4(4) ?
C13 C14 C15 O3 . . . . 179.6(3) ?
C13 C14 C15 C10 . . . . 0.5(4) ?
C11 C10 C15 O3 . . . . -178.6(2) ?
C9 C10 C15 O3 . . . . -0.7(3) ?
C11 C10 C15 C14 . . . . 0.6(4) ?
C9 C10 C15 C14 . . . . 178.5(2) ?
O2 C8 N1 C1 . . . . 176.4(3) ?
C7 C8 N1 C1 . . . . -2.8(3) ?
O2 C8 N1 C9 . . . . -5.1(5) ?
C7 C8 N1 C9 . . . . 175.7(2) ?
C2 C1 N1 C8 . . . . -177.3(3) ?
C6 C1 N1 C8 . . . . 1.6(3) ?
C2 C1 N1 C9 . . . . 4.2(4) ?
C6 C1 N1 C9 . . . . -176.9(2) ?
C10 C9 N1 C8 . . . . -110.2(3) ?
C10 C9 N1 C1 . . . . 68.1(3) ?
C14 C15 O3 C16 . . . . 9.3(4) ?
C10 C15 O3 C16 . . . . -171.6(2) ?
C16 C16 O3 C15 3_565 . . . 168.8(3) ?
